Production of S-(+)-ibuprofen from a nitrile compound by Acinetobacter sp. strain AK226.
S-(+)-2-(4'-Isobutylphenyl)propionic acid [S-(+)-ibuprofen] was produced from racemic 2-(4'-isobutylphenyl)propionitrile (Ibu-CN) by an isolated bacterial strain, Acinetobacter sp. strain AK226. Ammonium acetate, acetonitrile, or n-butyronitrile as a carbon source in the culture medium was effective for bacterial growth and induction of this activity. The optimum pH of the reaction was around 8.0. S-(+)-Ibuprofen formed from Ibu-CN by resting cells was present in a 95% enantiomeric excess. Acinetobacter sp. strain AK226 appeared to possess a nitrilase for Ibu-CN because 2-(4'-isobutylphenyl)propionamide was not detected in the reaction mixture and 2-(4'-isobutylphenyl)propionamide was not hydrolyzed to S-(+)-ibuprofen. Since S-(+)-ibuprofen was preferentially produced while the R enantiomer of Ibu-CN was left almost intact over the time course of the reaction, the putative nitrilase appeared to be highly specific for the S enantiomer of Ibu-CN.
Yamamoto
K
K
Pharmaceutical Research and Development Department, Asahi Chemical Industry Company Ltd., Miyazaki, Japan.
Ueno
Y
Y
Otsubo
K
K
Kawakami
K
K
Komatsu
K
K
D000150:Acinetobacter / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D007052:Ibuprofen / Q000378:metabolism*; D009570:Nitriles / Q000378:metabolism*; D013237:Stereoisomerism
D009570:Nitriles; D007052:Ibuprofen